Nickel-catalyzed reaction of arylzinc reagents with N-aromatic heterocycles: A straightforward approach to C-H bond arylation of electron-deficient heteroaromatic compounds

Journal of the American Chemical Society

Volumn 131, Issue 34, 2009, Pages 12070-12071

  Tobisu, Mamoru ^a   Hyodo, Isao ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; ARYLZINC REAGENTS; C-H BOND; CATALYTIC AMOUNTS; CATALYZED REACTIONS; CHEMICAL EQUATIONS; ELECTRON-DEFICIENT; ELECTROPHILIC SUBSTITUTIONS; HETEROAROMATIC COMPOUNDS; HETEROCYCLES; NICKEL COMPLEX;

CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; NICKEL ALLOYS;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; BORON DERIVATIVE; CARBON; CHLORIDE; DIHYDROQUINOLINE DERIVATIVE; ETHER; HETEROCYCLIC COMPOUND; HYDROGEN; NICKEL; NITROGEN; ORGANOLITHIUM COMPOUND; PYRAZINE; PYRIDINE; QUINOLINE; REAGENT; ZINC DERIVATIVE;

ADDITION REACTION; AROMATIZATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DEUTERON NUCLEAR MAGNETIC RESONANCE; ELECTRON; HIGH TEMPERATURE; HYDROGEN BOND; MOLECULAR PROBE; ONE POT SYNTHESIS; OXIDATION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 69349094999     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9053509     Document Type: Article

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34. In the catalytic arylation reactions and the reaction shown in eq 2, metallic precipitates were observed upon completion of the reactions. The metallic precipitates dissolved with gas evolution upon addition of aqueous HCl. On the basis of these observations, we currently believe that 5 is finally reduced to metallic Zn(0).